It is without a doubt characteristic for contemporary art scene that it can no longer be described as beautiful. Many writers and critics have thus turned to Kant’s notion of the sublime, in order to explain the aesthetic value of contemporary art works. Prima facie, this is not surprising considering how Kant explains the sublime, namely, as an experience of displeasure caused by the perceptual and imaginative incomprehensibility of the object, yet which we overcome by turning to the ideas of reason (such as ideas of freedom, morality, humanity etc.). Such an explanation of the sublime, as involving an element of perceptual and imaginative struggle, implicitly evokes the notion of ugliness. Also our experience of ugliness involves an element of frustration in grasping rich yet, chaotic and disintegrated structure of the object. Yet, what is distinctive for the sublime, in comparison to ugliness, that the feeling of displeasure in the sublime is merely of a transitory nature. Namely, Kant claims that displeasure of the sublime reveals a subjective purposive relationship between imagination and reason, which results in the feeling of pleasure. Kant’s explanation of the sublime raises the question as to why it is the case that even though both sublime and ugly objects are disordered and ill-adapted to our cognitive abilities, producing thereby the feeling of displeasure, yet that we should after all feel pleasure in the former, while not in the latter? Unfortunately, Kant does not offer an answer to this question. The same can be said about the contemporary discussions, which are primarily concerned with clarifying the distinction between the sublime and beauty, and little attention is given to Kant’s notion of the sublime in contrast to ugliness. This is not surprising considering that Kant does not discusses the notion of ugliness in his analysis of judgments of taste, even more; the concept of ugliness in Kant’s aesthetic is viewed by many as a seriously defective aesthetic notion. Contrary to such views I argue in this paper that a working concept of ugliness can be constructed from Kant’s analysis of the beautiful, and that even though the perceptual criteria of the sublime and ugliness appear to be similar, they are nevertheless theoretically and phenomenologically distinct aesthetic concepts. In addition, I apply my interpretation of the sublime to resolve certain issues that have been raised in accounting for the possibility of artistic sublimity.